(1'R,3S,4R)-3-[1'-((tert-butyldimethylsilyl)oxy)ethyl]-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone | 101905-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (1'R,3S,4R)-3-[1'-((tert-butyldimethylsilyl)oxy)ethyl]-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone
• 英文别名: (1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone；(1'R,3S,4R)-3-{1'-[(tert-butyldimethylsilyl)oxy]ethyl}-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone；(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one
• CAS: 101905-26-4；141781-32-0
• 化学式: C₂₆H₃₅NO₃Si
• 分子量: 437.654
• InChiKey: IUPGJSDLVQBZME-HLQJQHKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.15
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1'R,3S,4R)-3-[1'-((tert-butyldimethylsilyl)oxy)ethyl]-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone 在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以97%的产率得到(1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-4-(2'-phenylethenyl)-2-azetidinone
  参考文献：
  名称：

  从3-羟基丁酸酯完全合成硫霉素和相关β-内酰胺抗生素的手性中间体的立体和对映体控制的合成

  摘要：

  （1'的合成- [R，3小号，4小号） -和（1' - [R，3小号，4 - [R）-3-（1'-叔butyldimethylsilyoxyethyl）-4-羟甲基-2- azeidinone从乙基（小号）-3-羟基丁酸酯被报道。

  DOI：

  10.1039/c39850001433
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 sodium hydroxide 、 四氯化钛 、 三乙胺 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.08h， 生成 (1'R,3S,4R)-3-[1'-((tert-butyldimethylsilyl)oxy)ethyl]-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone
  参考文献：
  名称：

  Stereoselective synthesis of .beta.-lactams by condensation of titanium enolates of 2-pyridyl thioesters with imines

  摘要：

  A mild and versatile one-pot synthesis of beta-lactams has been performed by condensation of the easily generated titantium enolates of 2-pyridyl thioesters with imines employing chiral reaction partners. Both imines obtained from enantiomerically pure alkoxy aldehydes and the enolate derived from 3-hydroxybutyrate showed high diastereofacial preferences, efficiently transferring the stereochemical information to the stereocenters of the azetidinone ring. Advanced precursors of (+)-PS-5, (+)-PS-6, thienamycin, and 1-beta-methylthienamycin were prepared to illustrate the potential of this method. A H-1-NMR study of the enolization process and a tentative rationalization of the stereochemical results are presented.

  DOI：

  10.1021/jo00041a019

文献信息

• Synthesis of β-lactams by condensation of titanium enolates of 2-pyridylthioesters with imines. Influence of the imine structure on the trans/cis stereoselectivity
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi、Francesco Ponzini、Laura Raimondi

  DOI：10.1016/s0040-4020(01)87005-8

  日期：1994.2

  The condensation of the titanium enolates of C-2 alkyl substituted 2-pyridylthioesters with imines affords beta-lactams in trans/cis ratios that largely depend on the structure of the C-imine residue. Bulky and non-chelating heteroatom-containing groups lead to the formation of trans p-lactams, while sterically non-requiring or chelating groups favour the formation of the cia-products. On the basis of NMR evidences a rationale is proposed to account for the observed stereoselectivity.
• Asymmetric synthesis of (1'R,3R,4R)-4-acetoxy-3-[1'-((tert-butyldimethylsilyl)oxy)ethyl]-2-azetidinone and other 3-(1'-hydroxyethyl)-2-azetidinones from (S)-(+)-ethyl 3-hydroxybutanoate: formal total synthesis of (+)-thienamycin
  作者：Gunda I. Georg、Joydeep Kant、Harpal S. Gill

  DOI：10.1021/ja00238a023

  日期：1987.2